Five Overlooked Tips for Avoiding Cloud Migration Failure: How to Gain Buy-in from Employees and Set Realistic Expectations for Stakeholders

By Robin Morrison, Head of Agile Solutions and Michael Ryan, Director of Engineering

Kenzan + Sourced
7 min readApr 6, 2021

In a hurry to get to the cloud? Here’s what you need to keep in mind:

  • Tip 1: Gain momentum by addressing others’ points of view up front
  • Tip 2: Paint and communicate a vision for the future
  • Tip 3: Proactively manage expectations of business stakeholders
  • Tip 4: Integrate DevSecOps into your structure
  • Tip 5: Adopt agile now — even before cloud migration

Cloud migrations often pose daunting technical challenges, but the work doesn’t end there. Lack of attention to organizational and political considerations can also lead to suboptimal outcomes or or worse — outright failures.

At Kenzan, we work with company leaders who are eager to forge ahead to the cloud. However, there are choices companies make that can cause a cloud migration to fail before it ever gets off the ground. Here are some tips we’ve learned along that way that will help you ensure that your cloud migration takes off.

Tip One: Everyone is Not as Excited as You are About Adopting Cloud

To you, moving to the cloud means a bright future where enhanced organizational agility and superior quality let you win in the marketplace, free up money for new investments, and attract the best engineers in today’s tough labor market.

Unfortunately, not everyone will share your vision or your enthusiasm. Many will worry their day-to-day jobs will change or that they don’t have the skills and knowledge to handle what’s coming. Some will fear for their jobs and be tempted to slow walk or even sabotage your efforts. At the very least, cloud journeys transform the employee experience across the board, promising a radically different work environment for testers, developers, and managers. This can be jarring.

You can help make sure your vision becomes reality by having and communicating empathy for employees, finance leaders and other stakeholders. Take the time to understand their concerns so that you can address them upfront and sincerely.

  • Communicate early and often about training programs for all affected roles.
  • Emphasize that cloud technologies often result in better application performance and almost no downtime — which also means no late nights or weekend work trying to bring up systems that have crashed.
  • Stress how learning new technologies make employees more valuable in the marketplace.

Tip Two: Paint a Vision for the Future that Includes Benefits to the Company AND the Employees

For your vision to become a reality, you have to communicate it first. Communicate your vision for the cloud widely and often. Just as importantly, communicate in a way that helps everyone see how they can help to achieve — and benefit from — the cloud journey.

  • Describe how, when managing a public cloud rather than a virtualized data center, day-to-day work will change for employees — but it will be something exciting for them and their careers.
  • Talk about new roles that will be needed, like SRE (Site Reliability Engineering).
  • Ensure the cloud journey plan includes skill and role development training, and share widely that skills training is part of the cloud journey plan.

It’s crucial to back up your vision with concrete plans. Be armed with case studies and testimonials from engineers at other companies about how cloud migration has helped them learn new skills and improve their day-to-day work life. Honestly assess your team’s current skill sets, and lay out a detailed learning path for them. Identify the most tedious parts of their current workday and then show how cloud technology can eliminate them.

After these detailed training plans are developed, communicate them in multiple places. Discuss the training plans in All Hands meetings, and provide guidance on how managers can communicate the details in smaller team meetings and one-on-ones. Make sure to address how managers and employees can plan to sign up and participate in the training to make this feel real for everyone.

Tip Three — Proactively Manage Expectations of Business Stakeholders

In their excitement, company leadership can sometimes exaggerate expectations of a fast return on investment. The cloud transformation may even have been sold to senior management as a “quick win” with little risk and massive financial gain. Everyone assumes there will be radical savings in going to the cloud. The public cloud providers themselves emphasize savings in their marketing materials. You can and should save costs — but to do so you must implement cloud computing best practices across the business.

Ensure your transformation lasts longer than a quarter or two by explaining to business stakeholders the true scope of additional change and work required. Also explain that there are many more benefits to a cloud migration than just saving money. The ability to rapidly pivot to meet changing customer demands, improved quality and uptime of existing workloads, the financial benefits of operating expenses vs capital expenses, and the opportunity to recruit top technical talent are all widely-experienced benefits of cloud migrations.

  • Help VPs and business owners understand that simply moving workloads to the cloud will not automatically save money or achieve improved velocity. Changes in architecture and engineering practices will likely be required to achieve the full benefit of cloud technologies.
  • Help business stakeholders understand the difference between the various paths to cloud:
    Rehost means doing a “lift and shift” now and modernizing later. This strategy may result in minimal saves, or no savings at all, because existing applications haven’t been architected to truly take advantage of the cloud. Lift and shift efforts are best used as a precursor for future migration efforts.
    Re-factor / Re-architect means redesigning the architecture and code to build a cloud-native application. In this approach, you are essentially rewriting all or part of your application. An example would be moving from a monolithic application to a microservices architecture that can more easily take advantage of the cloud.
    Re-platform (sometimes referred to as “lift, tinker, and shift.”) means moving from on-premises to cloud with only modest enhancements to the application. These enhancements can include things like making specific pieces of your application more horizontally scalable.

Some types of workloads provide more opportunities for savings than others. The cloud lets you increase capacity to meet times of peak demand and then scale down when demand lessens — this is where cost savings can be found. If a workload experiences constant load, then there are fewer opportunities for savings.

Successfully scaling up and down to meet changes in demand often require changes to an application’s architecture. We typically find that a microservice architecture is often appropriate in these circumstances.

Tip Four: Integrate DevSecOps into your Engineering Processes

Enable teams to move faster in the cloud by building and integrating DevSecOps into your cloud pipeline. DevSecOps is not a role. Rather, it is a set of practices built on a philosophy of integrating security practices within the DevOps process itself. “Zero trust” security principles are a highly recommended offshoot of DevSecOps.

  • Beacheading is important. Trial and error can be expensive. You’ll need an initial team who understands the cloud to develop best practices and implement a good pipeline. Make sure each successive round of teams who join the migration know how to leverage it.
  • Implement devops processes by organizing your teams in a way that testing and deploying so that their work can be fully automated. Engineering time spent on wonky, one-off manual processes is time taken away from developing new features, infrastructure, and automations. This sort of work is de-motivating and frustrating for engineers.
  • What your organization receives for investing in DevSecOps is the ability to quickly respond to customer demand by rapidly and securely making changes to your infrastructure and applications.
  • Just as important as financial and competitive considerations is the ability to recruit top technical talent. Most technology workers want to work on the cloud! These skills are relevant to building their career. Offering work on cloud-native applications is a big recruiting tool if you want to attract top talent to your company.

Tip Five: Adopt Agile Now, Even Before Cloud Migration

IF you’re not Agile today, begin your Agile Transformation now.

Migrating to the cloud requires different processes than simply moving a data center to another location. You will not be able to exploit your new ability to deploy faster and improve time to market without also adopting an Agile workflow. Also, keep in mind that Agile methodologies require new training, processes, and transparency into work that may be just as much an object of uncertainty for employees as the cloud itself. So if you aren’t Agile already, start here!

Migrations benefit from having a solid and detailed plan, and most migrations follow a similar path. But in our experience, migration programs benefit from Scrum and other Agile methods. Cloud migrations have similar complexities compared to new software development — where seemingly simple applications become more complex, dependencies need to be managed, and close collaboration with business owners and end users is necessary. Most migrations experience frequent pivots and changes to the original plan. Constant focus on continuous improvement and supporting teams by removing impediments is as valuable to cloud migrations as it is to new software development.

You don’t have to learn through trial and error.

Just like with wheels, there’s no need to reinvent the cloud journey on your own. A trusted cloud consultant can help guide you through the myriad people and process considerations of your cloud migration. Having an experienced consultant along on the journey will help you gain the most from your cloud investment and ensure you have the organizational-readiness needed to capitalize on your newfound agility and scalability.